| Common Name |
4-Deoxyerythronic acid
| Description |
4-Deoxyerythronic acid is a normal organic acid present in human biofluids (PMIDs 2338430, 3829393, 3525594, 14708889, 1560100, 6725493), derived presumably from L-threonine. (PMID 2947647 ) It has been associated with uremia (PMID 1149237 ) and diabetes mellitus type 1. (PMID 2947647 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(+/-)-erythro-2,3-dihydroxybutyric acidHMDB
(R*,r*)-2,3-dihydroxy-butanoateHMDB
(R*,r*)-2,3-dihydroxy-butanoic acidHMDB
(R*,r*)-2,3-dihydroxybutanoateHMDB
(R*,r*)-2,3-dihydroxybutanoic acidHMDB
(R*,s*)-2,3-dihydroxybutanoateHMDB
(R*,s*)-2,3-dihydroxybutanoic acidHMDB
2,3-Dihydroxybutanoic acidHMDB
2,3-erythro-DihydroxybutyrateHMDB
2,3-erythro-Dihydroxybutyric acidHMDB
4-Deoxy-erythronateHMDB
4-Deoxy-erythronic acidHMDB
4-DeoxyerythronateHMDB
4-Deoxytetronic acidHMDB
erythro-2,3-Dihydroxybutyric acidHMDB
| Chemical Formlia |
C4H8O4
| Average Molecliar Weight |
120.1039
| Monoisotopic Molecliar Weight |
120.042258744
| IUPAC Name |
(2R,3R)-2,3-dihydroxybutanoic acid
| Traditional Name |
4-deoxyerythronic acid
| CAS Registry Number |
759-06-8
| SMILES |
C[C@@H](O)[C@@H](O)C(O)=O
| InChI Identifier |
InChI=1S/C4H8O4/c1-2(5)3(6)4(7)8/h2-3,5-6H,1H3,(H,7,8)/t2-,3-/m1/s1
| InChI Key |
LOUGYXZSURQALL-PWNYCUMCSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic oxygen compounds
| Sub Class |
Organooxygen compounds
| Direct Parent |
Sugar acids and derivatives
| Alternative Parents |
Short-chain hydroxy acids and derivatives
Beta hydroxy acids and derivatives
Monosaccharides
Fatty acids and conjugates
Alpha hydroxy acids and derivatives
Secondary alcohols
1,2-diols
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Beta-hydroxy acid
Short-chain hydroxy acid
Sugar acid
Monosaccharide
Hydroxy acid
Alpha-hydroxy acid
Fatty acid
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility454.0 mg/mLALOGPS
logP-1.2ALOGPS
logP-1.1ChemAxon
logS0.58ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.8 m3·mol-1ChemAxon
Polarizability10.74 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-0uk9-4900000000-e93ff8f7aad0f2c8fdeaView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0udr-9600000000-db7b2d4f0f4a450600e4View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0a4r-9000000000-c6f2a60b94ceef71fa3aView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-016r-9700000000-1e769b015c5e815e5fd1View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-05di-9200000000-320d571457b8c5b1a0acView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0ab9-9000000000-222ebdab55908e04bc53View in MoNA
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot Available
Normal
details
UrineDetected and Quantified5.0 +/- 3.0 umol/mmol creatinineAdlit (>18 years old)BothNormal
Geigy Scientific …
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022077
| KNApSAcK ID |
Not Available
| Chemspider ID |
17215960
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00498
| Metagene Link |
HMDB00498
| METLIN ID |
5484
| PubChem Compound |
13120901
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: URB602
References |
| Synthesis Reference |
Owen, L. N. Oxygenation of crotonaldehyde. Journal of the Chemical Society (1943), 563-8. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Kassel DB, Martin M, Schall W, Sweeley CC: Urinary metabolites of L-threonine in type 1 diabetes determined by combined gas chromatography/chemical ionization mass spectrometry. Biomed Environ Mass Spectrom. 1986 Oct;13(10):535-40. [PubMed:2947647 ]
- Bultitude FW, Newham SJ: Identification of some abnormal metabolites in plasma from uremic subjects. Clin Chem. 1975 Aug;21(9):1329-34. [PubMed:1149237 ]
|
PMID: 8944721